While the heater issue adds extra stress, addressing it promptly will protect you from further fines and penalties.

Debt is rarely a factor in their issue. the ultra wealthy I know  with a few exceptions have very limited debt.. to no debt. 

If the property was already listed on the MLS, I'd push back on the price relative to the comps.

It's unique and you could make this feature an amazing centerpiece and hero photo.Since you’re installing a mini-split, heat isn’t the issue—it’s all about guest experience and aesthetics.

They were abandoned and needed significant work which wasn't a huge issue but in terms of HUD owned properties i heard there can be significant processing periods.

May negative cashflow until fixed.3) Buy established business: assuming you mean something other than real estate related.

However, anything that impacts functionality like plumbing, HVAC, or safety issues should be handled before listing to avoid turning off potential renters/buyers.If you’re re planning to lease it, tenants will expect everything to be move-in ready before signing.

For example, ask about typical costs for HVAC repairs, plumbing issues, or roof work.- Use Historical Data: If the seller has accurate financials, their expense data can be invaluable.

What can I expect for timeline, potential issues, rough costs? 

If it's rehabbed nicely, then you will no issues finding a tenant.